#40KFaraway Day 2: Sleepless nights and long-haul flights


Day 2 of the 40K to Far Away challenge is in the books and I’m not going to lie: it feels good to be the mileage leader still despite only having used 7,500 points and $5.60. That said, “winner” is not a word I’d have used to describe myself last night. As Day 2 wraps up, all of our heroes had uncomfortable sleeping conditions and everyone has now taken or is taking a long-haul flight. Here’s where we stand.

¡Hola, Greg!

Based on Greg’s Instagram feed, he’s had a great day touring around Madrid after flying an overnight flight on Norwegian to get there. He looked surprisingly chipper in his arrival video despite the fact that he lost his butt pad early on. Perhaps he slept through most of the flight? I’m reminded of a coworker years ago who spent months in the hospital after a major burn accident. When he returned to work, I asked him if it still hurt. He replied, “Oh…..oooooonly when I’m awake.” Perhaps Greg’s strategy will be to sleep through the rest of his flights now that he’s lost his portable comfort.

It seems that Greg found himself some free sustenance thanks to his Business Platinum card, putting his WeWork benefit to use overseas (Note: This benefit is no longer available as of 1/1/20).


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WeWork provides refuge for a weary traveler (AKA me). #40kfaraway

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Then there was time for a little sight seeing in Madrid with a solo walking tour to take in the sights.

a large building with towers and a dome at night

Based on Greg’s tweet to end the evening, I think reader Greg accurately guessed about Greg’s accommodations for the night. Think fast: what kind of lodging did he line up in Madrid?

I’m guessing the big day tomorrow means that Greg is going to get going on one of the excursionist perks he set up in Lewisburg, WV on Day 1. But he isn’t really going to use that to fly across Europe, is he? I’d bet not: he hasn’t said, but I’m betting he’s positioning and picking up a big excursionist leg tomorrow across a large region. I may not be in the mileage lead for long.

Stephen avoids flushing it down the tubes

Stephen Pepper is taking the tortoise-and-hare game seriously, moseying his way to Newark on day 1 and spending what he says was a sleepless night at the airport. Having once slept landside at Newark airport, I can believe the sleeplessness. Hopefully he is somewhere in the sky right now in a nice comfy middle seat wrestling for an arm rest :-).

That said, he almost got an even slower start: not realizing he needed a visa to transit Canada by air, Stephen’s trip nearly went down the tubes. Thankfully he had saved that on Day 1. However, Air Canada fittingly sat him next to the toilet to remind him of how he almost flushed his chances to win this thing.

He’s been tight-lipped about his next stop. Once I knew he wasn’t flying to Brazil (I had a theory about this), I thought for sure Stephen might try to book the Aeroplan Canadian hopper. But he’s apparently got other things in mind. This cryptic tweet led at least one reader on Facebook to ponder the possibility of two Frequent Miler authors ending up in the same city at the same time.

I am very curious as to where Stephen will wind up next as he is thus far nowhere near where I predicted.

Nick’s night did not go right

As for me, I had a great evening on Honolulu and a not-great-night before continuing onward to try to build on my mileage lead before Greg wakes up.

The hour delay in my arrival to Honolulu immediately cramped my style (or was it the 10+ hours in economy class by that point?). I went looking for The Bus, Oahu’s public bus system — which sells an unlimited day pass (valid until 3am the next morning) for $5.50. Unfortunately, that was delayed also — as was the transfer I needed. Eventually, but much later than I’d hoped, I made it to the start of the Lanikai Pillboxes hike, which looks to be one of the most scenic points on Oahu. Unfortunately, because of a combination of the 25lbs on my back, cloudy conditions that didn’t aid in getting extra sunlight, and the start of some rain (making the rocks I’d needed to sometimes scramble over kind of slippery), I didn’t make it all the way to the top. However, I was still grinning ear to ear at having gotten on a plane for 7500 points + $5.60 and then spent $5.50 on a bus pass to get here.


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Afterwards, I met up with some points and miles enthusiasts in Honolulu at Uncle Clay’s House of Pure Aloha — a must-stop in Honolulu.

a group of people posing for a photo

Unfortunately, things took a slight turn for the worse after parting ways with my friends.

You may have noticed in my packing video I had a hotel key in my bag. About a month ago, I spent two nights at the Hyatt Place Waikiki Beach. As it turned out, I ended up being up until 4 or 5am both nights working in the lobby and nobody there said anything to me (the lobby is huge, so there are plenty of places to camp out and not really be noticed). Since nobody said anything to me last time, I figured that if there was a Hyatt Place key sitting on the table next to my computer as I worked, security would be even less likely to bother me. My plan was to spend the entire night working at the Hyatt Place and then head to the airport in the morning and sleep on my next flight.

a bottle and a can of soda on a table
There’s my Hyatt Place key, which I had intentionally kept after my stay last month.

Unfortunately, I overestimated my ability to make a mad sprint at ORD airport to make my connection, scramble up a small mountain hike with a 25lb backpack, and stay awake for 30 hours on 2-4 hours sleep for the previous couple of nights. I was a mess. I kept falling asleep while trying to write a post, so I eventually moved to that high top table in the background where I would have to stand. When I fell asleep standing for the second time and nearly fell over (and I know the desk agent saw me stumble the second time), I decided that it was time to pack it up: I had unrealistic goals. It was almost 2am. With my bus pass set to expire at 3am and a bus trip to the airport, including one transfer on the way, scheduled to have me arriving at the airport a couple of minutes before 3am, I decided it was time to wave the white flag and just head to the airport. I had to walk a couple of blocks in the rain to pick up the bus, but then I was on.

The crowd on the bus at 2am is exactly what you would expect at 2am in any major city. At least a couple of folks were drunk, strung out, or both. Again, there were no surprises given the hour: the city bus at 2am wouldn’t be my transportation mode of choice in any city.

All of a sudden, the bus doors opened and I woke up. Still on the bus. Shoot! What time is it? 2:44am. I knew right away but pulled up Google maps to confirm that we were well beyond where I was supposed to transfer. UghAt this point, it was just me and the folks who appeared to be on drugs left on the bus and we were reaching the final stop — some sort of transit center. I was both annoyed with myself for falling asleep and incredibly thankful that my Tumi backpack with laptop, DSLR camera, credit cards, and money was still sitting on the seat next to me undisturbed. I think that says something: riding the bus late at night didn’t seem unsafe, though I wouldn’t put that theory to the test a second time.

The transit center seemed more sketchy. Google maps told me that the next option to get to the airport would leave at about 3:15am — after my bus pass would have expired and longer than I was excited about sitting around at the transit center. Budget-wise, I probably should have sucked it up and waited for the next bus. A single ride ticket is only $2.75 (which makes the day pass worthwhile if you will ride the bus more than once in a day). Instead, I called an Uber and spent $10.43 to get to the airport. I almost immediately regretted it, but c’est la vie.

Unfortunately, Honolulu airport isn’t open all night. So I spent the next couple of hours here, just outside of the airport by the curb.

a backpack on a bench

It was a cozy slab. If you find dark, dirty, and uncomfortable cozy, that is. I don’t.

On the bright side, since I was sitting by the curb, I got a front row seat for the rain and wind show that played overnight.

Just before 5am, I saw people walking in via another entrance and I found a much more comfortable chair, using my backpack as an ottoman and getting about 2 hours of solid, restful sleep.

a man lying on a chair

Then, upon getting through security, I got a message from my friend Susan who was at Uncle Clay’s above. She reminded me that you don’t need to be flying inter-island to access the inter-island terminal. That meant that in addition to the crummy IASS lounge (which only has a couple of Keurigs and soda / juice), you can access the Hawaiian Air Plumeria Lounge by the inter-island gates. They have pour-in ramen, half sandwiches, olives and veggies, beer, wine, coffee, etc. Three cheers for the breakfast of champions.

a plate of food on a table

Then I boarded my next flight to get a little further away for not-many-more miles. Luckily, I got fed on this flight — the beef curry was surprisingly good.

a tray of food on a table

After a night like last night, I awoke in my chair at Honolulu airport very much looking forward to the Rising Sun. My hope for the day is that I don’t get claustrophobic too easily. Care to venture a guess as to where I’m going next? I say going in continuous form because I’m posting this live from 30,000+ feet.

Will Day 3 be the day that Greg makes a big move? Will I extend my lead? Where in the world is Stephen Pepper heading?

Stay tuned as I think things are about to get interesting…

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